diff --git a/eclipse-language-servers/org.springframework.tooling.boot.ls/src/org/springframework/tooling/boot/ls/DelegatingStreamConnectionProvider.java b/eclipse-language-servers/org.springframework.tooling.boot.ls/src/org/springframework/tooling/boot/ls/DelegatingStreamConnectionProvider.java
index 42dc2682f..ba755affd 100644
--- a/eclipse-language-servers/org.springframework.tooling.boot.ls/src/org/springframework/tooling/boot/ls/DelegatingStreamConnectionProvider.java
+++ b/eclipse-language-servers/org.springframework.tooling.boot.ls/src/org/springframework/tooling/boot/ls/DelegatingStreamConnectionProvider.java
@@ -148,7 +148,10 @@ public class DelegatingStreamConnectionProvider implements StreamConnectionProvi
 		private String host;
 		private String urlScheme = "https";
 		private String port = "443";
-		private boolean keepChecking = false;
+		private boolean keepChecking = true; 
+			//keepChecking defaults to true. Boot dash automatic remote apps should override this explicitly.
+			//Reason. All other 'sources' of remote apps are 'manual' and we want them to default to
+			//'keepChecking' even if the user doesn't set this to true manually.
 
 		public RemoteBootAppData(String jmxurl, String host) {
 			super();
@@ -246,6 +249,11 @@ public class DelegatingStreamConnectionProvider implements StreamConnectionProvi
 					app.setUrlScheme(urlScheme);
 				}
 			}
+			//keepChecking attribute added in STS 4.2.1
+			if (list.size()>=5) {
+				String keepChecking = list.get(4);
+				app.setKeepChecking("true".equals(keepChecking));
+			}
 			return app;
 		}
 		throw new IllegalArgumentException("Invalid remote app data: "+incomingData);
diff --git a/headless-services/spring-boot-language-server/src/main/java/org/springframework/ide/vscode/boot/java/handlers/RemoteRunningAppsProvider.java b/headless-services/spring-boot-language-server/src/main/java/org/springframework/ide/vscode/boot/java/handlers/RemoteRunningAppsProvider.java
index 91425f4e2..f11c91a2c 100644
--- a/headless-services/spring-boot-language-server/src/main/java/org/springframework/ide/vscode/boot/java/handlers/RemoteRunningAppsProvider.java
+++ b/headless-services/spring-boot-language-server/src/main/java/org/springframework/ide/vscode/boot/java/handlers/RemoteRunningAppsProvider.java
@@ -35,7 +35,10 @@ public class RemoteRunningAppsProvider implements RunningAppProvider {
 		private String host;
 		private String urlScheme = "https";
 		private String port = "443";
-		private boolean keepChecking = false;
+		private boolean keepChecking = true;
+			//keepChecking defaults to true. Boot dash automatic remote apps should override this explicitly.
+			//Reason. All other 'sources' of remote apps are 'manual' and we want them to default to
+			//'keepChecking' even if the user doesn't set this to true manually.
 
 		public String getJmxurl() {
 			return jmxurl;